N-[(S)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine | 1354546-18-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(S)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine
• CAS: 1354546-18-1
• 化学式: C₅₈H₇₂N₄O₁₂
• 分子量: 1017.23
• InChiKey: UTWUZWJTKMHNSZ-OUEPNEBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  74.0
• 可旋转键数：
  27.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  223.07
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-[(S)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 24.0h， 以50%的产率得到N-[(S)-3-(α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Mannose Derived Immunomodulating Adamantyltripeptides

  摘要：

  A novel class of mannosylated adamantyltripeptides, general formula of which is alpha-Man-OCH2CH(CH3)CO-AdGly-L-Ala-D-isoGln, were prepared, characterized, and their possible immunomodulatory properties investigated in some preliminary tests in vivo. All newly synthesized glycopeptides comprise in their structure the adamantylglycyl moiety linked to the dipeptide L-Ala-D-isoGln, as well as mannose. Adjuvant activity of mannosylated adamant-2-yl tripeptides was tested in the mouse model using ovalbumin as an antigen and in comparison to the peptidoglycan monomer (PGM, beta-D-GlcNAc-(1 -> 4)-D-MurNAc-L-Ala-D-isoGln-mesoDAP(epsilon NH2)-D-Ala-D-Ala). (doi: 10.5562/cca1827)

  DOI：

  10.5562/cca1827
• 作为产物：
  描述：

  9-fluorenylmethyloxycarbonyl-(adamant-1-yl)glycine 在 1-辛硫醇 、 1-羟基苯并三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 117.0h， 生成 N-[(S)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Mannose Derived Immunomodulating Adamantyltripeptides

  摘要：

  A novel class of mannosylated adamantyltripeptides, general formula of which is alpha-Man-OCH2CH(CH3)CO-AdGly-L-Ala-D-isoGln, were prepared, characterized, and their possible immunomodulatory properties investigated in some preliminary tests in vivo. All newly synthesized glycopeptides comprise in their structure the adamantylglycyl moiety linked to the dipeptide L-Ala-D-isoGln, as well as mannose. Adjuvant activity of mannosylated adamant-2-yl tripeptides was tested in the mouse model using ovalbumin as an antigen and in comparison to the peptidoglycan monomer (PGM, beta-D-GlcNAc-(1 -> 4)-D-MurNAc-L-Ala-D-isoGln-mesoDAP(epsilon NH2)-D-Ala-D-Ala). (doi: 10.5562/cca1827)

  DOI：

  10.5562/cca1827